Ethyl 4-isocyanatobenzoate → 1-Methylsufonyl-n-(4-ethoxycarbonylphenyl)spiro[indoline-3,4'-piperidine]-1'-carboxamide

HRID 2298959Notes

Reaction equation

HRID 2298959 reaction equation
[CH3:1][S:2]([N:5]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:7]2([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6]1)(=[O:4])=[O:3].[N:19]([C:22]1[CH:32]=[CH:31][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:24][CH:23]=1)=[C:20]=[O:21]>ClCCl>[CH3:1][S:2]([N:5]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:7]2([CH2:8][CH2:9][N:10]([C:20]([NH:19][C:22]3[CH:23]=[CH:24][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:31][CH:32]=3)=[O:21])[CH2:11][CH2:12]2)[CH2:6]1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 589805Ethyl 4-isocyanatobenzoateHCID 111400731-(Methylsulfonyl)spiro[indoline-3,4'-piperidine]

Product 1

HCID 180048821-Methylsufonyl-n-(4-ethoxycarbonylphenyl)spiro[indoline-3,4'-piperidine]-1'-carboxamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-methylsulfonyl-spiro[indoline-3,4′-piperidine] (2.66 g, 10 mmol) in dichloromethane (50 mL), was added ethyl 4-isocyanatobenzoate (1.91 g, 10 mmol) at room temperature. The resulting solution was stirred for four hours during which time precipitation occurred. The mixture was evaporated to remove dichloromethane, and then was suspended in methanol (20 mL), filtration followed by washing with cold methanol gave 1500 as a white solid (4.56 g, 100%)

Workup

  1. customThe mixture was evaporated
  2. customto remove dichloromethane
  3. filtrationfiltration
  4. washby washing with cold methanol

Sources & evidence

ORD record
ord-5fecc41214e241e5bf5dc820e916b2b5
Source dataset
uspto-grants-2002_12
Patent number
US06495559B2

Reaction notes

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